Benzoyl chloride → HCID 5073926、化合物

HRID 2217326ノート

反応式

HRID 2217326 の反応式
I.[S:2]1[C:6]2[CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:5]=2[N:4]=[C:3]1[NH2:14].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[S:2]1[C:6]2[CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:5]=2[N:4]=[C:3]1[NH:14][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

4

反応物 2

HCID 7412Benzoyl chlorideHCID 49796119HCID 49796119、化合物

生成物 1

HCID 5073926HCID 5073926、化合物収率 56.7%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

To a mixture of Indeno[1,2-d]thiazol-2-ylamine hydroiodide 1a (100 mg; 0.32 mmol) in pyridine (2 mL) was added benzoyl chloride (0.12 mL; 0.96 mmol) dropwise. The mixture was then agitated at 80° C. in a sealed tube overnight. The mixture was allowed to cool to room temperature and the solvent removed in vacuo. The residue was taken up into ethyl acetate and the extract allowed to stir with 2M sodium carbonate solution for 2 hours at room temperature. The organic layer was then washed with brine solution, dried over sodium sulfate and concentrated in vacuo. The crude product was chromatographed on silica gel (eluent: 10% ethyl acetate/hexanes to 40% ethyl acetate gradient) to provide 53 mg of N-(8H-Indeno[1,2-d]thiazol-2-yl)-benzamide 2. EI-HRMS m/e calcd for C17H12N2OS 292.0670, found 292.0666.

後処理

  1. temperatureto cool to room temperature
  2. customthe solvent removed in vacuo
  3. stirringto stir with 2M sodium carbonate solution for 2 hours at room temperature
  4. washThe organic layer was then washed with brine solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was chromatographed on silica gel (eluent: 10% ethyl acetate/hexanes to 40% ethyl acetate gradient)

出典と根拠

ORDレコード
ord-271011d1bfc34483899205deb4f6ce5a
出典データセット
uspto-grants-2008_08
特許番号
US07407977B2

反応ノート

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